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Details

Stereochemistry ABSOLUTE
Molecular Formula C18H16N8O7S3.2Na
Molecular Weight 598.544
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of CEFTRIAXONE SODIUM ANHYDROUS

SMILES

[Na+].[Na+].[H][C@]12SCC(CSC3=NC(=O)C(=O)[N-]N3C)=C(N1C(=O)[C@H]2NC(=O)C(=N/OC)\C4=CSC(N)=N4)C([O-])=O

InChI

InChIKey=LTFQVRWXHBGEMZ-BBJOQENWSA-L
InChI=1S/C18H18N8O7S3.2Na/c1-25-18(22-12(28)13(29)23-25)36-4-6-3-34-15-9(14(30)26(15)10(6)16(31)32)21-11(27)8(24-33-2)7-5-35-17(19)20-7;;/h5,9,15H,3-4H2,1-2H3,(H5,19,20,21,23,27,29,31,32);;/q;2*+1/p-2/b24-8-;;/t9-,15-;;/m1../s1

HIDE SMILES / InChI

Description

Ceftriaxone is a broad-spectrum cephalosporin antibiotic with a very long half-life. Ceftriaxone is a bactericidal agent that acts by inhibition of bacterial cell wall synthesis. Ceftriaxone has activity in the presence of some beta-lactamases, both penicillinases and cephalosporinases, of Gram-negative and Gram-positive bacteria. It is approved for the treatment of lower respiratory tract infections, acute bacterial otitis media, skin infections, urinary tract infections, pelvic inflammatory disease, bacterial septicemia, bone and joint infections, intraabdominal infection, meningitis, and surgical prophylaxis. Common adverse reactions include erythema multiforme, Stevens-Johnson syndrome, toxic epidermal necrolysis, pseudomembranous enterocolitis, hemolytic anemia, hypersensitivity reaction, kernicterus, renal failure, and lung injury. Vancomycin, amsacrine, aminoglycosides, and fluconazole are incompatible with Ceftriaxone in admixtures. Precipitation of Ceftriaxone-calcium can occur when Ceftriaxone for Injection is mixed with calcium-containing solutions in the same intravenous administration line.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
2.38 µM [Ki]
0.23 µM [Ki]
4.39 µM [Ki]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
CEFTRIAXONE
Curative
CEFTRIAXONE
Curative
CEFTRIAXONE
Curative
CEFTRIAXONE
Curative
CEFTRIAXONE
Curative
CEFTRIAXONE
Curative
CEFTRIAXONE
Curative
CEFTRIAXONE
Curative
CEFTRIAXONE
Curative
CEFTRIAXONE

Cmax

ValueDoseCo-administeredAnalytePopulation
82 μg/mL
0.5 g single, intravenous
CEFTRIAXONE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
478 μg × h/mL
0.5 g single, intravenous
CEFTRIAXONE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
8.7 h
0.5 g single, intravenous
CEFTRIAXONE plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
5%
0.5 g single, intravenous
CEFTRIAXONE plasma
Homo sapiens

Doses

AEs

OverviewOther

Other InhibitorOther SubstrateOther Inducer



Drug as victim

Tox targets

PubMed

Sample Use Guides

In Vivo Use Guide
The usual adult daily dose is 1 to 2 grams given once a day (or in equally divided doses twice a day) depending on the type and severity of infection. The total daily dose should not exceed 4 grams. For the treatment of uncomplicated gonococcal infections, a single intramuscular dose of 250 mg is recommended.
Route of Administration: Other
In Vitro Use Guide
ceftriaxone MIC cutoff of 8 μg/ml against E. coli, Klebsiella spp., and P. mirabilis is an excellent predictor of extended-spectrum β-lactamase (ESBL) production, with a positive predictive value and negative predictive value approaching 100% and 99.5%, respectively.